Methyl iodide → 2-Propenoic acid, 3-(2-methylphenyl)-, methyl ester, (2E)-

HRID 1066353Notes

Reaction equation

HRID 1066353 reaction equation
[CH3:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5][C:6]([OH:8])=[O:7].[CH2:13]1CCN2C(=NCCC2)CC1.CI>CN(C=O)C.CCOCC>[CH3:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1/[CH:4]=[CH:5]/[C:6]([O:8][CH3:13])=[O:7]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 983063-(2-Methylphenyl)prop-2-enoic acid

Product 1

HCID 101763492-Propenoic acid, 3-(2-methylphenyl)-, methyl ester, (2E)-Yield 98.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To 2-methylcinnamic acid (100 g; 617 mmol) in 1.2L of DMF was added DBU (112.6 g; 740 mmol) and 15 min later methyl iodide (131.3 g; 925 mmol) and left overnight. The solution was diluted in ether and washed with HCl (10%), H2O and brine. The solvent was removed to give 106.8 g of the title compound.

Workup

  1. washwashed with HCl (10%), H2O and brine
  2. customThe solvent was removed

Sources & evidence

ORD record
ord-0af96d35bd824cada2a2c12c097024eb
Source dataset
uspto-grants-2001_06
Patent number
US06242493B1

Reaction notes

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